EP2076478B1 - Verfahren zur herstellung fluorierter olefine - Google Patents
Verfahren zur herstellung fluorierter olefine Download PDFInfo
- Publication number
- EP2076478B1 EP2076478B1 EP07863530A EP07863530A EP2076478B1 EP 2076478 B1 EP2076478 B1 EP 2076478B1 EP 07863530 A EP07863530 A EP 07863530A EP 07863530 A EP07863530 A EP 07863530A EP 2076478 B1 EP2076478 B1 EP 2076478B1
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- European Patent Office
- Prior art keywords
- catalyst
- reaction
- stream
- conversion
- fluorinated
- Prior art date
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- 150000001336 alkenes Chemical class 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 189
- 239000003054 catalyst Substances 0.000 claims description 143
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 54
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 41
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 34
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- 229910052739 hydrogen Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Chemical class 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 150000005828 hydrofluoroalkanes Chemical class 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 7
- 229910001512 metal fluoride Inorganic materials 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 claims description 2
- VRVIDSRWPUGFBU-UHFFFAOYSA-N 2-chloro-1,1,1-trifluoropropane Chemical compound CC(Cl)C(F)(F)F VRVIDSRWPUGFBU-UHFFFAOYSA-N 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 27
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 24
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- 150000001335 aliphatic alkanes Chemical class 0.000 description 16
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 description 15
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 15
- 238000006722 reduction reaction Methods 0.000 description 15
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical class O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000001276 controlling effect Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229910052593 corundum Inorganic materials 0.000 description 5
- 238000007033 dehydrochlorination reaction Methods 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- -1 propene Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910001845 yogo sapphire Inorganic materials 0.000 description 5
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 3
- 229910000792 Monel Inorganic materials 0.000 description 3
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical class FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical class FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 2
- CDOOAUSHHFGWSA-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropene Chemical compound FC=CC(F)(F)F CDOOAUSHHFGWSA-UHFFFAOYSA-N 0.000 description 2
- RRUCZSCEAWFDBM-UHFFFAOYSA-N 1-bromo-2,3,3,3-tetrafluoroprop-1-ene Chemical compound BrC=C(F)C(F)(F)F RRUCZSCEAWFDBM-UHFFFAOYSA-N 0.000 description 2
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 2
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical compound FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 description 2
- 229910020186 CeF4 Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- PFFGXVGPSGJOBV-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropane Chemical compound FCCC(F)(F)F PFFGXVGPSGJOBV-UHFFFAOYSA-N 0.000 description 1
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021564 Chromium(III) fluoride Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- QVYYOKWPCQYKEY-UHFFFAOYSA-N [Fe].[Co] Chemical compound [Fe].[Co] QVYYOKWPCQYKEY-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- YFKIWUQBRSMPMZ-UHFFFAOYSA-N methane;nickel Chemical compound C.[Ni] YFKIWUQBRSMPMZ-UHFFFAOYSA-N 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229910001120 nichrome Inorganic materials 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
Definitions
- 1,2,3,3,3-Pentafluoropropene-1 is hydrogenated using the same reactor as in Example 1 using a feed rate of 14.6 lb/h for a total of 64 hours.
- the average hydrogen feed rate is 25 liters per minute.
- Samples are taken at various points along the series of reactors to follow the percent conversion and selectivity. After the second reactor, the conversion is about 54%. While after the fourth reactor, the conversion is 100% with the selectivity for CF 3 CHFCH 2 F of 98%.
- the temperature of the gases immediately exiting the reactors is 99°C for the first reactor, 95°C for the second reactor, 173°C for the third reactor, and 104°C for the fourth reactor.
- the maximum temperature in any reactor is about 240°C.
- the first bath is maintained at 59°C
- the second bath is maintained at 116°C.
- the column bottoms containing sulfuric acid and HF are recycled back to the extraction tower until the HF concentration is greater than 10 wt% HF. Subsequently, the sulfuric acid and HF mixture is charged into a 2 gallon Teflon ® vessel. The mixture is heated to about 140°C to vaporize and flash off HF, which is collected. The collected HF product contains 6000 ppm water and 217 ppm sulfur. The sulfuric acid contains about 500 ppm of total organic carbon.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (8)
- Verfahren zur Herstellung eines fluorierten Olefins als Produkt, bei dem man:(a) einen Einsatzstrom, der fluoriertes Olefin und Wasserstoff als Reaktanten umfasst, mit einer ersten Menge eines Katalysators kontaktiert, wobei die Reaktanten mit einer ersten Umwandlungsrate in ein Hydrofluoralkan umgewandelt werden und ein erster Ausgangsstrom, der das Hydrofluoralkan, nicht umgesetztes fluoriertes Olefin und Wasserstoff umfasst, anfällt;(b) den ersten Ausgangsstrom mit einer zweiten Menge eines Katalysators kontaktiert, wobei das nicht umgesetzte fluorierte Olefin mit einer zweiten Umwandlungsrate in ein Hydrofluoralkan umgewandelt wird, wobei die zweite Katalysatormenge größer ist als die erste Katalysatormenge und die zweite Umwandlungsrate größer ist als die erste Umwandlungsrate;(c) mindestens einen Teil des Hydrofluoralkans aus dem Kontaktierungsschritt (b) dehydrohalogeniert, wobei ein Produktstrom, der ein fluoriertes Olefin und HF als Produkt umfasst, anfällt; und(d) gegebenenfalls das HF von dem Produktstrom trennt.
- Verfahren nach Anspruch 1, bei dem man in Schritt (d) ferner mindestens einen Teil des Produktstroms mit Schwefelsäure kontaktiert, wobei HF aus dem Produktstrom extrahiert wird.
- Verfahren nach Anspruch 2, bei dem bei dem Kontaktieren in Schritt (d) ein Schwefelsäure-Austragsstrom, der mindestens einen Teil des HF aus dem Produktstrom enthält, anfällt und man bei dem Verfahren ferner mindestens einen Teil des Schwefelsäure-Ausgangsstroms durch einen Extraktionsturm rezykliert.
- Verfahren nach Anspruch 1, bei dem die Reaktanten ein Fluorpropen mit drei bis sechs Fluorsubstituenten umfassen.
- Verfahren nach Anspruch 1, bei dem das Hydrofluoralkan Chlortrifluorpropan (H-FCKW 244), Pentafluorpropan (H-FKW 245) und/oder (H-FKW 236) umfasst.
- Verfahren nach Anspruch 1, bei dem das Produkt F2C=CFCF3 und/oder CFH=CFCF3 umfasst.
- Verfahren nach Anspruch 1, bei dem die Umwandlungsschritte (a) und (b) jeweils die Verwendung von kohlenstoffgeträgertem Palladium umfassen.
- Verfahren nach Anspruch 1, bei dem der Dehydrohalogenierungsschritt eine katalysierte Reaktion unter Beteiligung eines Katalysators aus der Gruppe bestehend aus einem oder mehreren fluorierten Metalloxiden, Metallfluoriden, kohlenstoffgeträgerten Übergangsmetallen und Kombinationen davon umfasst.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/588,464 US7560602B2 (en) | 2005-11-03 | 2006-10-27 | Process for manufacture of fluorinated olefins |
PCT/US2007/082601 WO2008057794A1 (en) | 2006-10-27 | 2007-10-26 | Process for the manufacture of fluorinated olefins |
Publications (3)
Publication Number | Publication Date |
---|---|
EP2076478A1 EP2076478A1 (de) | 2009-07-08 |
EP2076478B1 true EP2076478B1 (de) | 2012-10-03 |
EP2076478B2 EP2076478B2 (de) | 2020-11-25 |
Family
ID=39201461
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP07863530.7A Active EP2076478B2 (de) | 2006-10-27 | 2007-10-26 | Verfahren zur herstellung fluorierter olefine |
Country Status (8)
Country | Link |
---|---|
US (2) | US7560602B2 (de) |
EP (1) | EP2076478B2 (de) |
JP (1) | JP5588174B2 (de) |
KR (2) | KR20140090702A (de) |
CN (1) | CN101553453B (de) |
ES (1) | ES2394870T5 (de) |
RU (1) | RU2457195C2 (de) |
WO (1) | WO2008057794A1 (de) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101553453B (zh) | 2013-05-29 |
US20070179324A1 (en) | 2007-08-02 |
ES2394870T5 (es) | 2021-07-27 |
RU2008122213A (ru) | 2010-04-27 |
WO2008057794A1 (en) | 2008-05-15 |
US7786333B2 (en) | 2010-08-31 |
RU2457195C2 (ru) | 2012-07-27 |
US7560602B2 (en) | 2009-07-14 |
ES2394870T3 (es) | 2013-02-06 |
JP2010508294A (ja) | 2010-03-18 |
KR20140090702A (ko) | 2014-07-17 |
US20090209791A1 (en) | 2009-08-20 |
CN101553453A (zh) | 2009-10-07 |
JP5588174B2 (ja) | 2014-09-10 |
EP2076478A1 (de) | 2009-07-08 |
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